Thianthrene

Thianthrene is an organic compound with the formula C12H8S2. This sulfur-containing compound is a yellow solid. Thianthrene is a building block to a family of heterocyclic compounds that are used in organic synthesis and pharmaceutical research.

Structure and Synthesis

Thianthrene is a polycyclic aromatic hydrocarbon (PAH) that consists of two benzene rings fused to a central dithiin ring. The molecule is planar and exhibits a large π-bonding system, which contributes to its stability and aromaticity.

The synthesis of thianthrene involves the reaction of diphenyl disulfide with sodium in ammonia. This reaction yields thianthrene and sodium sulfide.

Applications

Thianthrene and its derivatives have been used in various applications in organic synthesis. For example, thianthrene-5-oxide is a useful reagent in the synthesis of sulfones. Thianthrene itself can be used as a protecting group for aldehydes and ketones in organic synthesis.

In pharmaceutical research, thianthrene derivatives have been studied for their potential antibacterial and antifungal properties.

Safety

Like many PAHs, thianthrene is expected to be a low to moderate hazard for human health. However, specific safety data for thianthrene is not widely available. As with all chemicals, it should be handled with appropriate safety precautions.

See Also

• Polycyclic aromatic hydrocarbon
• Organic synthesis
• Pharmaceutical research